


Interlude: A Damned Good Time Together

by reginahalliwell



Series: Some Kind of Goodbye [6]
Category: Gilmore Girls
Genre: Alternate Universe - Canon Divergence, F/M, Fix-It, Mild Smut, Stand Alone
Language: English
Status: Completed
Published: 2016-12-29
Updated: 2016-12-29
Packaged: 2018-09-13 02:47:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,031
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9103108
Author URL: https://archiveofourown.org/users/reginahalliwell/pseuds/reginahalliwell
Summary: After movie night with Lorelai, Rory and Jess get up to some hijinks in Rory's bedroom.This is an interlude from the Some Kind of Goodbye series that can also be read as a standalone fic. For that, all you need to know is that this is an alternate late season 4 where Rory and Jess are back together post-Nag Hammadi and trying to make it work with Lorelai's support.





	

**Author's Note:**

> The title and last line are a reference to the final passage of Ernest Hemingway's The Sun Also Rises:
> 
> "Oh, Jake," Brett said, "we could have had such a damned good time together." 
> 
> ...
> 
> "Yes," I said. "Isn’t it pretty to think so?"
> 
> ~
> 
> There's additional irony here if you've read The Sun Also Rises, but it's not necessary to appreciate this fic.

Rory and Jess didn't feel comfortable doing much of anything in her room initially, despite Lorelai’s decision to go to bed right after School of Rock ended. She seemed just as uncomfortable with the situation as Rory was pretending not to be. 

Jess had kindly offered to sleep on the couch with Lorelai in earshot, hoping she wouldn’t take him up on it. Sure enough, Lorelai took the high road and insisted that that was silly, and there was no reason he couldn’t stay in Rory’s room. Rory offered her mother a small smile as a thank-you, but Lorelai’s eyes told her she was hoping nothing would happen in her daughter’s childhood bedroom that night.

The two curled up on Rory’s twin bed to read, Jess having pulled a random novel off her shelf. It turned out to be The Sun Also Rises.

“Let me guess, poor Ernest didn’t make the cut for dorm room books?”

She bowed her head and grimaced playfully. “Oops. Sorry, I just can’t seem to get into it.”

“It’s fine. We both gave it a try, right? Doesn’t mean he has to be your favorite… although I think the good people of the Nobel and Pulitzer Prize committees seem to disagree with you.”

“What, like you’ve ever cared what authority figures think?”

“Eh, you’re right.”

“I do like the idea of it. I want to travel, you know, now that my mom and I have seen some of Europe, I want to make that part of my life. Maybe be an ex-pat like good old Hemingway and friends. We saw the bar in Paris where he did a lot of his writing, you know?”

“That’s cool. You stop and have a drink?”

“Well, a coffee. We had to pace ourselves with the alcohol.”

“Just as well. I can’t see you two knocking them back in the middle of day with huge backpacks on. I’m trying to imagine it, but it’s just not working.”

“Very funny. We stayed in Paris for a while, actually, so we left our backpacks at the hostel. I did almost topple over in Venice, though. Did you know they don’t have any cars there and you basically have to walk everywhere? I didn’t. And it was the summer, and I brought way too many books. It wasn’t pretty.”

“Sheesh. I want to hear all about it sometime. The trip of a lifetime.”

“Maybe we’ll go. Someday. A literary tour of Europe.”

He smiled sadly, not sure he could really hope they would be together long into the future to do things like that. He wanted it more than anything, but it wasn’t in his control.

“For now, though, let’s have Ernest offer the one skill you do seem to appreciate.”

“What’s that?”

“I’ll read to you, and poor Ernest’s words will lull you right to sleep.”

Rory cackled louder than she wanted to, even though it wasn’t late.

“Sounds good to me. I can’t get through more than five pages of that thing without dozing off.”

“Perfect,” Jess agreed, turning the pages and curling up against Rory, her head on his shoulder with her eyes closed as he started to read from the last chapter of the book. 

Though his voice made Hemingway’s words sound much more interesting to her, Rory was already out only minutes later. He finished the book anyway, its closing lines about the impossibility of love and a happy future together perhaps describing their own relationship in another universe.

~

It was Jess who stirred first, untangling himself from Rory to get up and use the bathroom. The clock in the kitchen read 2:17 am, and the house was completely silent as he padded barefoot over the hard floors. 

When he walked back through her bedroom door, Rory turned to look up at him, wiping at her bleary eyes as he came back into focus. 

He climbed back into bed with her, warming his feet back up on hers under the covers. 

“Having dreams of Paris?” he asked.

“Good dreams, yes. About Europe, no.” The glint in her eye told him everything she wasn’t saying. 

“Huh.”

“Yeah. What can I say, it’s weird having you in my childhood bed with me, when everything in me wants to do things with you that are distinctly adult in nature.”

“Rory, is that your way of telling me that you want me?”

“Maybe.”

“Now? Here?” They hadn’t really gotten anywhere close to having sex, and he hadn’t thought that it might happen here. He assumed his place was where it would all eventually go down. 

Rory blushed prettily, even in the dark. He could hear the anxiety in her voice. “Not, not with my mom right upstairs. But maybe we could—” she broke off, not really sure what she was asking for.

“Nothing you can’t look your mom in the eyes after,” he suggested, knowing her well.

She nodded, the desire in her eyes evident as he leaned in to kiss her. Jess’s hand gripped her hip, holding her close against him so she could feel his growing arousal. She moaned quietly as his tongue slipped into her mouth, her lips moving against his to a mess of breathy groans. Her chest pressed against his as well, and he could feel her breasts heaving with her gasps as their kisses escalated. 

Threading her fingers in his hair, Rory’s eyes rolled back as she felt him move down her neck, laving the spot where her pulse was hammering under her skin. He heard her whisper his name, desperately, like a plea.

“I know,” he said, his hand raising from her hip to trail his fingers gently down her neck and trace the outline of one nipple under her sleep shirt, feeling it harden even more under her. 

Something that sounded like a whimper came out of Rory, and she drew his face back to hers, kissing him fiercely and willing him to understand her agony, which she knew he shared…if the erection pressing into her abdomen was any indication. 

“Here,” he whispered, pulling her partially underneath him so he could fit one leg between hers. When she ground against him instinctively, his body responded involuntarily with a thrust against her. 

He hissed, the pleasant feeling derailed by the squeak of Rory’s bed underneath them. Her eyes went wide as she clearly panicked. “Bad idea,” he admitted. 

“No, a great idea,” Rory countered, “Just—later. At your place. Tonight.”

“Careful, Rory. A guy could get used to this.”

He felt her body shake with silent laughter. 

“I’m getting pretty used to this, too,” she said, pulling a tendril of her short hair out of her face. When she tried to settle back down, it was clear that Rory was too frustrated to be comfortable. She was sure he was too; Jess’s erection was still poking at his boxers, which wasn’t exactly conducive to immediate sleep.

“Can I?” she asked, looking down as though she couldn’t even meet his eyes.

“You want to?” he wondered aloud.

“I mean, I just, we haven’t. But you’re—and I want to help…” she stopped and started, trying to rationalize something that he definitely didn’t need to be convinced into doing.

“You don’t have to,” he offered. “It’ll go down eventually.”

“No, I want to.” He could tell she was nervous, but the look in her eyes told him there was also desire there, and curiosity. 

Jess nodded, and Rory moved back towards him, kissing him as she tentatively moved her hand down his chest, across his abs, which fluttered under her touch, and into his boxers. It was one thing holding him in her hand in the dark, without seeing what she was doing. This would be much scarier in the light of day.

She touched him lightly, feeling the length of him and testing all the surfaces and textures there. Rory could feel that certain motions made Jess quake against her, others made him jerk, and more still made him gasp and moan quietly beneath her untried movements.

She had no idea what she was doing, but it seemed to be going well. She could feel some moisture at the end of his erection when she moved her hand there. This all felt so illicit but also right. Rory knew this was a good step forward, and she was enjoying seeing this side of Jess. He was so vulnerable in her hand like this, his body bending to her touch, his pleasure a result of her actions. 

Jess began to pant, desperate and aching for some release, and Rory didn’t know how to get him there. He looked her in the eyes, reached into his boxers and covered his hand with her own. He adjusted her grip and moved her hand beneath his in practiced motions. It was arousing to see him take such clear direction, knowing exactly what he wanted. She knew that he had done this hundreds of times by himself, and he guided her movements with a surety that reinforced this in her mind. She could see the moment it happened, in his eyes, the sound he made, and of course the spurt of liquid that splattered her hand and was now wetting his boxers. 

She had done this. She had held him in her hand, stroked and worked him until she made him come. Now she knew what he liked, and she could feel a new intimacy growing between them, that they were doing this together. They might not be naked right now but she had touched him all the same.

“God, Rory, that was amazing,” he whispered. 

“Yeah?” she asked, hopeful that she hadn’t messed anything up.

“Yeah,” he confirmed, kissing her again and imbuing the embrace with gratitude and love and more.

She could see that he was exhausted now, from that whole ordeal and from the knowledge that he had to get up in only a few hours to go help Luke.

“Let’s go to bed, Casanova,” Rory joked. 

“I kind of think we already did…” Jess commented, and of course Rory blushed back at him. 

“Let’s go back to sleep, then,” she amended. 

Jess rallied, pulling himself up onto one elbow to look at her, one eyebrow raised. “You think I’m going to leave you like that after you just gave me an amazing handjob? Hell no.”

“I don’t want to wake my mom up, Jess,” she insisted. 

“If I can be quiet, you can be quiet,” he said, trying to rationalize. She always responded best if he gave her suitable reasons. Pro/con lists and whatnot.

“Really, you don’t have to. We can wait until tomorrow night.”

Instead of responding, Jess moved a hand down to Rory’s abdomen, feeling her stomach jump at his touch. 

“Jess,” she pleaded quietly, not sure she could control herself. 

Her pelvis jerked up toward his touch as Jess ran his hand in between her legs, feeling the hair through her underwear. He had touched her here over her jeans, that night of the Distillers concert. Even then he could feel that she was wet for him under her clothes, that their long make-out session in his car had a very visceral response in her. 

His fingers rubbed over where he knew she was most sensitive, and she jerked and clutched at him, his touch sending shockwaves through her. He moved his hand down, pressing into her just barely through her underwear, feeling the wetness there that signaled her own desire. 

“Jeez, Rory, do you know what this does to me?”

“I have some idea,” she offered, riding the high of giving him an orgasm with her hand just a minute ago. 

He continued his ministrations, the barrier of her cotton underwear becoming more soaked and slippery as his fingers aroused her even more, teasing and playing with her.

“Ugh,” she groaned, her brow furrowing. “Don’t stop. Please.”

“Over or under?” he asked, sure that she would let him continue but only outside her clothes. 

“Under,” she surprised him. “Under is good.”

He looked her in the eyes to make sure she was fine with that, and when all he saw there was desire, not fear or concern, Jess let himself push the cotton aside and feel her with his bare hand. She was slick with arousal, nearly shaking with desire, and each swipe of his fingers dragged little gasps out of her. She closed her legs on his hand and grabbed him at the shoulder, desperate for more of the feelings he was bringing her. 

He too tried out different motions, testing which ones got the best reactions out of her, though they all seemed to please Rory. He could see that her eyes were shut tightly, her lip between her teeth as she struggled to not make a sound.

Jess adjusted so he could use two hands, rubbing in circles as his fingers plunged in and out of her, gently at first, then more forcefully as she responded to the motions. She was shocked at how deliciously pleasurable this was—her own touch couldn’t hold a candle to what Jess was making her feel. 

It was easy to let herself go with him, when there was no one else around and it was just Jess and Rory. She could just be her, just love him, and want him, and joke with him, and nothing else mattered. And right now, all that mattered was what Jess was doing with his fingers. God, his hands. She didn’t think she had ever appreciated hands as much as she did right now. 

It was almost enough, almost. Jess had a good rhythm, and the thrusts of his fingers were pushing her closer and closer to ecstasy with every second that passed. She did as he had, and snuck her own hand in, guiding Jess’s fingers to a pattern of movements that felt best to her, but he pulled his one hand away as his other continued thrusting gently into her, and he chose to let her touch herself instead, so he could watch her. 

“You are so beautiful, Rory.”

Their eyes met as she swirled two fingers around the excited bundle of nerves that was begging for release. 

“I love you, Jess.”

“I love you, too,” he responded, leaning up to kiss her urgently as his fingers continued, and he pressed up against her insides as he thrust, applying pressure where she needed it. 

That did it. A few more circles of her fingers, and Jess’s words and his thrusts and his eyes, and Rory couldn’t hold it back any longer. The wave of pleasure washed over her, and Jess’s fingers took over where hers were exhausted, helping her ride it out and extend the pleasure. He gentled his movements, taking care not to over-stimulate her, and Rory softened into the mattress as she came down off her amazing high. 

Jess pulled out his fingers, wrinkled and wet, and wiped his hand on his boxers. They were already ruined, so what did it matter? He could change into some spare clothes he still had at Luke’s when he went over in the morning… in three hours. 

“That was…” she began, then lost the words to describe what she felt. 

“It wasn’t your first time, right?”

She looked at him quizzically. He knew she had never--

“I mean, that wasn’t the first time you came?”

“Oh, no, I guess not. It’s only happened a couple of times, though, and nothing like that.”

“That good, huh?”

“Don’t get cocky, now. Knowing us, it’s not going to be that easy the whole way. One of us is bound to screw something up soon.”

“Well it may not be in the sex department, because we’ve never had issues in that area. It’s pretty much the only issue we haven’t had, except for at Kyle’s party, I mean.”

“I don’t think that counts as a sex problem. More a location problem and a communication problem. But I don’t want to talk about that right now.”

“What do you want to talk about?” he asked, assuming they would need to discuss everything that just happened, and how he felt about it, and what she thought about it, and all the potential ramifications of all this, and what she was going to say to her mother, and more.

Instead, she sighed happily. “I just want to fall asleep with you holding me. And then I want to repeat this, very soon. Tomorrow night, if possible. I know you were planning to work a night shift, but I will definitely answer a booty call if you get off and want to…you know. Get off.”

“Did you just come on to me?”

“Why not? We both literally just came onto each other.”

“Wow, college Rory is crude.”

“What can I say, higher education has corrupted me.”

He chuckled and kissed her hair. “I’d love to repeat any and all of this, as early and often as you like. You will never hear me complaining about getting to make you feel like that. It’s a rush, isn’t it?”

She nodded against him, fading quickly. 

“You want me to wake you up when I leave to cover at Luke’s?” he asked, seeing that their conversation was definitely over. Her eyes were having trouble staying open, and her arms had gone limp around him. 

“Nope. Need sleep. Must replenish energy.”

“I get that,” he said, feeling exhausted himself, but very glad he hadn’t just passed out as soon as he came. “Well, whenever you get up, I’ll have coffee ready for you at Luke’s. All you can drink.”

“Yes!” she hissed, eyes still closed. “I knew you would come through as my coffee supplier again.”

“That’s what I’m here for. Coffee, orgasms, and book sharing.”

“Love you, Jess.”

“Love you, Rory,” he responded, and then let her sleep. He had two hours and twenty-six minutes until he had to wake up to open Luke’s, but he wouldn’t take back a minute of what he and Rory had just shared. A damned good time together indeed, and not so impossible as it had once seemed.


End file.
